Ethyl 3-oxovalerate → 2-(3-chlorophenyl)-6-ethylpyrimidin-4(3H)-one

HRID 1508671노트

반응식

HRID 1508671 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](=[NH:7])[NH2:6].O=[C:12]([CH2:19][CH3:20])[CH2:13][C:14](OCC)=[O:15].C[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:6][C:14](=[O:15])[CH:13]=[C:12]([CH2:19][CH3:20])[N:7]=2)[CH:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 78656Ethyl 3-oxovalerateHCID 2041443-Chloro-benzamidineHCID 10942334Sodium Methoxide

생성물 1

HCID 1356311952-(3-chlorophenyl)-6-ethylpyrimidin-4(3H)-one수율 39%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A 1-L round bottomed flask was charged with 3-chlorobenzimidamide (23.9 g, 154 mmol, 1 eq.), ethyl 3-oxopentanoate (27.8 g, 193 mmol, 1.25 eq.), and ethanol (500 mL). To the mixture was added sodium methoxide (10.0 g, 185 mmol, 1.20 eq.). The resulting mixture was stirred under reflux for 20 hr. After cooling to room temperature, the mixture was evaporated under reduced pressure to 50 mL. The residual slurry was cautiously treated with 2N HCl (219 mL). Solid was collected by filtration and washed with water followed by ether to afford 2-(3-chlorophenyl)-6-ethylpyrimidin-4(3H)-one (9.3 g, 39% yield), which was carried forward into the next step without further purification. 1H NMR (CD3OD, 500 MHz) δ 8.07 (s, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.62-7.58 (m, 1H), 7.52 (t, J=8.0, Hz, 1H), 6.27 (s, 1H), 2.66 (q, J=7.5 Hz, 2H), 1.29 (t, J=7.5 Hz, 3H).

후처리

  1. temperatureunder reflux for 20 hr
  2. customthe mixture was evaporated under reduced pressure to 50 mL
  3. additionThe residual slurry was cautiously treated with 2N HCl (219 mL)
  4. filtrationSolid was collected by filtration
  5. washwashed with water

출처 및 근거

ORD 기록
ord-551c6cbdc10d4da1b0cad0385f179416
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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